CN111944143A - Bio-based polyarylether resin containing furan ring structure and preparation method thereof - Google Patents

Bio-based polyarylether resin containing furan ring structure and preparation method thereof Download PDF

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CN111944143A
CN111944143A CN202010777270.9A CN202010777270A CN111944143A CN 111944143 A CN111944143 A CN 111944143A CN 202010777270 A CN202010777270 A CN 202010777270A CN 111944143 A CN111944143 A CN 111944143A
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ring structure
furan ring
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bio
polyarylether resin
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CN111944143B (en
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王锦艳
蹇锡高
刘程
柳承德
张守海
翁志焕
胡方圆
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Dalian University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C08G65/4031—(I) or (II) containing nitrogen
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used

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Abstract

The invention provides a furan ring structure-containing bio-based polyarylether resin and a preparation method thereof. The invention uses the bio-based monomer to replace petroleum-based monomer to prepare the polyaryletherketone resin, and can effectively deal with petroleum crisis.

Description

Bio-based polyarylether resin containing furan ring structure and preparation method thereof
The application is divisional application of application number 201810109871.5, application date 2018, 02 month 05, and invention name "furan ring structure-containing bio-based polyarylether resin and preparation method thereof".
Technical Field
The invention belongs to the technical field of polymer science, relates to a novel polyarylether resin and a preparation method thereof, and particularly relates to a furan ring structure-containing bio-based polyarylether resin and a preparation method thereof.
Background
The polyaryletherketone resin is a novel high-temperature-resistant high-performance engineering plastic, has the advantages of high heat-resistant grade, excellent mechanical property, electrical property and radiation resistance, chemical resistance, fatigue resistance, impact resistance, creep resistance, wear resistance, flame retardance and the like, and is widely applied to many high and new technical fields of aviation, electronic information, energy and the like. However, conventional polyaryletherketone resins have been developed based on non-renewable petroleum resources. With the annual increase of the crude oil consumption in the world and the gradual decline of the petroleum reserves, the shortage of petroleum resources is bound to become the limitation of the further development of high-performance engineering plastic polyaryletherketone resin. Therefore, the research and development of the bio-based polyaryletherketone resin have very important time significance and will become the inevitable trend of future development.
Furan dicarboxylic acid (FDCA) is a biobased diacid [ LewkowskiJ. Synthesis, Chemistry and Applications of 5-Hydroxymethyl-furfuel and Its Derivatives Cheminams.2001, 34(2):37 ], similar in structure to terephthalic acid (PTA), prepared by catalytic oxidation of the biomass derivative 5-Hydroxymethylfurfural (HMF) [ Willem P.Dijkman, Daphene E.Groothuis, Marco W.Fraje.AngewamInt Ed.2014,53(25): 6515-. With the increasing maturity of bio-based furandicarboxylic acid production technologies, numerous studies have been attempted using furandicarboxylic acid instead of terephthalic acid, such as polyesters containing furan ring structures (PEF, PPF, PBF) [ Knoop R JI, Vogelzang W, Haveren J.journal of Polymer Science Part A: Polymer chemistry.2013,51(19): 4191) 4199, epoxy resins [ Deng J, Liu X, Li C, Jiang Y, Zhu J.RSC adv.2015,5(21): 30 15939], polyimides, and the like. The research results show that the introduction of the furan ring structure does not reduce the performance of the material, and the furan ring structure is obviously improved in some aspects.
The subject group is dedicated to the research of petroleum-based polyaryletherketone resin, develops a series of polyaryletherketone resin with excellent performance, and is widely applied to the industries of aerospace, electronic and electrical, petroleum exploitation and the like. In view of the above, the invention starts from furandicarboxylic acid, prepares bio-based and dihalo-benzophenone monomers containing furan ring structures, creatively utilizes the bio-based dihalo-benzophenone monomer containing furan ring structures furan-2, 5-bis (4-fluorophenyl) ketone (BFBF), develops a class of bio-based homopolymerization (or copolymerization) polyaryletherketone resin containing furan ring structures, and aims to prepare polyaryletherketone resin by using bio-based monomers instead of petroleum-based monomers so as to deal with petroleum crisis and environmental problems. At present, no public report is found.
Disclosure of Invention
The invention relates to a furan ring structure-containing bio-based polyaryletherketone resin and a preparation method thereof. The preparation method comprises the step of carrying out nucleophilic polycondensation reaction on furan-2, 5-di (4-fluorophenyl) ketone (BFBF) as a biological group monomer containing a furan ring structure and one or more of a dihydric phenol monomer and dihalobenzophenone to prepare the polyaryletherketone resin containing the furan ring structure and the biological group homopolymerization (or copolymerization).
The technical scheme of the invention is as follows:
a furan ring structure-containing bio-based polyarylether resin has the following chemical structure:
Figure BDA0002618903930000031
wherein m is more than or equal to 1, and n is more than or equal to 0;
Figure BDA0002618903930000032
the structure of (1) is as follows:
Figure BDA0002618903930000033
Figure BDA0002618903930000034
the structure of (1) is as follows:
Figure BDA0002618903930000035
Figure BDA0002618903930000036
Figure BDA0002618903930000041
Figure BDA0002618903930000051
Figure BDA0002618903930000052
one or a combination of two or more of them; wherein, R, R1、R2、R3、R4、R5、R6、R7、R8The structure is as follows: H. f, Cl, Br, I, CN, NH2、Cr+1H2r+2、CrH2r+1、CrH2r+1COOH、OCrH2r+1、CF3、
Figure BDA0002618903930000053
One or more than two of the (a) and (b) are mixed, and r is more than or equal to 1; r, R1、R2、R3、R4、R5、R6、R7And R8The same or different;
Figure BDA0002618903930000054
the structure of (1) is as follows:
Figure BDA0002618903930000055
Figure BDA0002618903930000056
Figure BDA0002618903930000061
one or more than two of the components are mixed.
A preparation method of furan ring structure-containing bio-based polyarylether resin comprises the following polymerization reaction formula and steps:
Figure BDA0002618903930000062
wherein m is more than or equal to 1, n is more than or equal to 0, and X is F, Cl, Br or I;
Figure BDA0002618903930000063
the structure of (1) is as follows:
Figure BDA0002618903930000064
Figure BDA0002618903930000065
the structure of (1) is as follows:
Figure BDA0002618903930000066
Figure BDA0002618903930000067
Figure BDA0002618903930000071
Figure BDA0002618903930000081
Figure BDA0002618903930000082
one or a combination of two or more of them; wherein, R, R1、R2、R3、R4、R5、R6、R7、R8The structure is as follows: H. f, Cl, Br, I, CN, NH2、Cr+1H2r+2、CrH2r+1、CrH2r+1COOH、OCrH2r+1、CF3、
Figure BDA0002618903930000083
One or more than two of the (a) and (b) are mixed, and r is more than or equal to 1; r, R1、R2、R3、R4、R5、R6、R7And R8The same or different;
Figure BDA0002618903930000084
the structure of (1) is as follows:
Figure BDA0002618903930000085
Figure BDA0002618903930000086
Figure BDA0002618903930000087
one or more than two of the components are mixed.
The specific synthesis steps are as follows:
under the protection of inert gas, containing furan ring structure
Figure BDA0002618903930000088
Of a dihalogen monomer of
Figure BDA0002618903930000089
Structural dihydric phenol monomer, containing
Figure BDA0002618903930000091
Mixing a double-halogen monomer with a structure with alkali, adding a strong-polarity aprotic solvent and an azeotropic solvent, carrying out water treatment on a reaction system at the temperature of 110-150 ℃, removing the azeotropic solvent after reacting for 0.5-3 h, heating the reaction system to 160-200 ℃, reacting for 5-10 h, slowly pouring a viscous solution into a settling agent to obtain a fibrous substance, filtering, boiling the fibrous substance with boiling water for 10-24 h, and drying the fibrous substance at the temperature of 100-150 DEG CDrying the crude product for 10-24 h at 90-150 ℃ under vacuum condition to constant weight to obtain a crude polyaryletherketone resin product containing furan ring structure bio-based homopolymerization or copolymerization; dissolving a crude polyaryletherketone resin product in a good solvent, wherein the mass ratio of the crude product to the good solvent is 1: 5-1: 35, filtering, settling filtrate in a settling agent, and sequentially filtering, drying by blowing and drying in vacuum to obtain the refined furan ring structure-containing bio-based polyaryletherketone resin;
wherein the molar ratio of the phenolic hydroxyl group to the halogen is 1: 0.9-1: 1.1, and the molar ratio of the alkali to the phenolic hydroxyl group is 1: 1.2-1: 2.2; the volume ratio of the azeotropic solvent to the mixed solvent is 1: 1-1: 3.
The structure containing furan ring
Figure BDA0002618903930000092
The reaction formula and the preparation method of the double-halogen monomer are as follows:
Figure BDA0002618903930000093
wherein, X has the structure: F. one of Cl, Br and I;
to be provided with
Figure BDA0002618903930000094
For example, the specific synthesis steps are as follows:
firstly, synthesizing a furan diformyl chloride intermediate, namely adding bio-based furan dicarboxylic acid and thionyl chloride into a reaction vessel with magnetic stirring according to the mass ratio of 0.2: 1-1: 1, and simultaneously adding a small amount of strong polar aprotic solvent DMF (1% of the volume of the thionyl chloride), wherein the reaction temperature is as follows: 60-100 ℃, reaction time: 2-6 hours. After the reaction is finished, cooling the system to room temperature, removing redundant thionyl chloride, and carrying out vacuum sublimation to obtain a white furan diformyl chloride FDCC crystal;
and secondly, under the protection of inert gas, taking the furan ring structure-containing bio-based intermediate FDCC and fluorobenzene as raw materials, taking Lewis acid as a catalyst, and reacting in a low-boiling-point organic solvent to prepare the target monomer. Wherein the mol ratio of FDCC to fluorobenzene is 1: 2-1: 5, the volume ratio of the low-boiling-point organic solvent to FDCC is 1: 3-1: 5, and the mol ratio of the Lewis acid catalyst to FDCC is 1: 2-1: 5; the reaction temperature is 25-100 ℃, and the reaction time is 10-24 h; after the reaction is finished, the mixture is settled in a settling agent, and the furan ring structure-containing bio-based dihalobenzophenone monomer BFBF is obtained after suction filtration, purification and drying.
Wherein, the inert gas is one of nitrogen, argon and helium.
The Lewis acid is one or the mixture of more than two of boron trichloride, boron tribromide, boron trifluoride and aluminum trichloride.
The low boiling point organic solvent is one or the mixture of more than two of chloroform, dichloromethane, dichloroethane and acetonitrile.
The alkali is one or more of potassium carbonate, cesium carbonate, sodium hydroxide and potassium hydroxide.
The strong polar aprotic solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone and sulfolane.
The azeotropic solvent is one or more of toluene, xylene and chlorobenzene.
The good solvent is one or a mixture of more than two of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, sulfolane and chloroform.
The settling agent is one or more of methanol, ethanol, isopropanol, acetone and water.
The invention has the beneficial effects that: the bio-based monomer furan dicarboxylic acid is used for designing and synthesizing a bio-based dihalobenzophenone monomer containing a furan ring structure, and then a series of excellent-performance bio-based homopolymerization (or copolymerization) polyaryletherketone resins containing the furan ring structure are prepared. The resin not only effectively deals with the petroleum crisis, but also can be regulated and controlled to obtain the target resin with high temperature resistance, dissolubility, easy processing and excellent mechanical property so as to meet the actual requirement.
Drawings
FIG. 1 is a 1H-NMR spectrum of a furan ring structure-containing bio-based polyaryletherketone resin PFBEK.
FIG. 2 is a 1H-NMR spectrum of a furan ring structure-containing bio-based polyaryletherketone resin PFBEK.
FIG. 3 is FTIR spectra of furan ring structure-containing bio-based polyaryletherketone resins PFBEK and PFDEK.
Detailed Description
The following examples further illustrate the preparation method and properties of the furan ring structure-containing bio-based polyaryletherketone resin of the present invention, but do not represent the limitation of the present patent.
EXAMPLE 1 preparation of PFBEK
Under the protection of nitrogen atmosphere, a furan ring structure-containing bio-based monomer BFBF (10mmol,3.1227g), 9, 9-bis (4-hydroxyphenyl) fluorene BPF (10mmol,3.5042g) and anhydrous potassium carbonate K are added into a three-neck flask with mechanical stirring2CO3(14mmol,1.9023g) is dissolved in a mixed solvent of 4ml of sulfolane, 1ml of N-methyl pyrrolidone and 10ml of toluene, the mixture is reacted for 4h at 125-160 ℃, the toluene in the mixed system is evaporated, then the temperature is raised to 195 ℃ for reaction for 10h, the viscous solution is poured into hot water to obtain a white fibrous polymer, the fibrous polymer is boiled by boiling water for 8-12 h, and then the fibrous polymer is dried to constant weight to obtain a white crude product of the furan ring structure-containing bio-based polyaryletherketone resin PFBEK. Dissolving the crude product in chloroform according to a certain proportion, filtering, settling the filtered solution in absolute ethyl alcohol, and then sequentially filtering, drying by blowing and drying in vacuum to obtain the refined target product PFBEK with the yield of 99.9%. The nuclear magnetic and infrared characteristics of PFBEK are shown in the attached figures 1 and 2, and the heat resistance characteristics are shown in the table 1.
The structural formula is as follows:
Figure BDA0002618903930000121
EXAMPLE 2 preparation of polymer PFDEK
In a three-neck flask with mechanical stirring under the protection of nitrogen atmosphereAdding a furan ring structure-containing bio-based monomer BFBF (10mmol,3.1227g), phthalazinone biphenyl DHPZ (10mmol,2.3824g) and anhydrous potassium carbonate K2CO3(14mmol,1.9023g) is dissolved in a mixed solvent of 3ml of sulfolane, 2ml of N, N-dimethylacetamide and 10ml of toluene, the mixture is reacted for 4h at 125-160 ℃, the toluene in the mixed system is evaporated, then the temperature is raised to 195 ℃ for reaction for 10h, finally the viscous solution is poured into hot water to obtain a white fibrous polymer, the fibrous polymer is boiled by boiling water for 8-12 h, and then the fibrous polymer is dried to constant weight to obtain a white crude product of the furan ring structure-containing bio-based polyaryletherketone resin PFDEK. And dissolving the crude product in chloroform according to a certain proportion, filtering, settling the filtered solution in absolute ethyl alcohol, and sequentially filtering, drying by blowing and drying in vacuum to obtain a refined target product PFDEK with the yield of 99.9%. The nuclear magnetic and infrared characterization of PFDEK is shown in fig. 3 and fig. 2, and the thermal performance test data is shown in table 1.
Figure BDA0002618903930000131
Table 1 shows the results of thermal performance tests of the furan ring structure-containing bio-based polyaryletherketone resins PFBEK and PFDEK.
Figure BDA0002618903930000132

Claims (8)

1. A furan ring structure-containing bio-based polyarylether resin is characterized in that the structural formula is as follows:
Figure FDA0002618903920000011
2. the furan ring structure-containing bio-based polyarylether resin of claim 1, wherein the polyarylether resin has a weight average molecular weight of 63045 g/mol.
3. A method for preparing the furan ring structure-containing bio-based polyarylether resin of claim 1 or 2, comprising the steps of:
under the protection of nitrogen atmosphere, adding 10mmol of furan ring structure-containing bio-based monomer BFBF, 10mmol of phthalazinone biphenyl DHPZ and anhydrous potassium carbonate K into a three-neck flask with mechanical stirring2CO3Dissolving 14mmol of the crude product in a mixed solvent of 3ml of sulfolane, 2ml of N, N-dimethylacetamide and 10ml of toluene, reacting for 4 hours at 125-160 ℃, evaporating to remove the toluene in the mixed system, then heating to 195 ℃ for reaction for 10 hours, finally pouring the viscous solution into hot water to obtain a white fibrous polymer, boiling with boiling water for 8-12 hours, and drying to constant weight to obtain a white crude product of the furan ring structure-containing bio-based polyaryletherketone resin;
wherein the furazane ring structure-containing bio-based monomer BFBF is
Figure FDA0002618903920000021
Said phthalazinone biphenyl DHPZ is
Figure FDA0002618903920000022
4. The method for preparing the furan ring structure-containing bio-based polyarylether resin of claim 3,
Figure FDA0002618903920000023
the specific synthesis steps are as follows:
firstly, synthesizing a furan diformyl chloride intermediate: adding bio-based furandicarboxylic acid and thionyl chloride into a reaction container with magnetic stirring according to the mass ratio of 0.2: 1-1: 1, and simultaneously adding a strong polar aprotic solvent DMF which is 1% of the volume of the thionyl chloride, wherein the reaction temperature is as follows: 60-100 ℃, reaction time: 2-6 hours; after the reaction is finished, cooling the system to room temperature, removing redundant thionyl chloride, and carrying out vacuum sublimation to obtain a white furan ring structure-containing bio-based intermediate FDCC crystal;
under the protection of inert gas, taking a furan ring structure-containing bio-based intermediate FDCC and fluorobenzene as raw materials, taking Lewis acid as a catalyst, and reacting in a low-boiling-point organic solvent to prepare a target monomer; wherein the mol ratio of FDCC to fluorobenzene is 1: 2-1: 5, the volume ratio of the low-boiling-point organic solvent to FDCC is 1: 3-1: 5, and the mol ratio of the Lewis acid catalyst to FDCC is 1: 2-1: 5; the reaction temperature is 25-100 ℃, and the reaction time is 10-24 h; after the reaction is finished, the precipitate is settled in a settling agent, and the product is obtained after suction filtration, purification and drying.
5. The method for preparing the furan ring structure-containing bio-based polyarylether resin of claim 4, wherein the settling agent is one or more of methanol, ethanol, isopropanol, acetone and water.
6. The method for preparing the furan ring structure-containing bio-based polyarylether resin of claim 4, wherein the inert gas is one of nitrogen, argon and helium.
7. The method for preparing the furan ring structure-containing bio-based polyarylether resin of claim 4, wherein the Lewis acid is one or a mixture of two or more of boron trichloride, boron tribromide, boron trifluoride and aluminum trichloride.
8. The method for preparing the furan ring structure-containing bio-based polyarylether resin of claim 4, wherein the low boiling point organic solvent is one or a mixture of two or more of chloroform, dichloromethane, dichloroethane and acetonitrile.
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